Synthesis of Some Mono-, Bis- NH-substituted-1,4-Benzoquinones

Abstract

The preparation of new mono- and bis- NH-substituted-1,4-benzoquinones, namely 2,5-bis(5,6-dimethylbenzo[d]thiazol-2-ylamino)cyclohexa-2,5-diene-1,4-dione (3), 2,5-bis(3-(2-methylpiperidin-1-yl)propylamino)-3-chlorocyclohexa-2,5-diene-1,4-dione (6), 2-(4-tert-butylbenzylamino)-3,5,6-trichlorocyclohexa-2,5-diene-1,4-dione (9), 2-(4-fluorophenylamino)-6-tert-butylcyclohexa-2,5-diene-1,4-dione (12) is reported. The synthesis of new quinone derivatives (3, 6, 9, 12) have been carried out from the reactions between quinones (p-benzoquinone (1), 2,6-dichloro-1,4-benzoquinone (4), tetrachloro-1,4-benzoquinone (7), 2-tert-butyl-1,4-benzoquinone (10)) and different amines (2-Amino-5,6-dimethylbenzothiazole (2), N-(3-aminopropyl)-2-pipecoline (5), 4-tert-butylbenzylamine (8), 4-fluoroaniline (11)). The new compounds were characterized by elemental analysis, mass spectrometry, IR, 1H-NMR, 13C-NMR spectroscopy.